Integrated process for the production of 1-chloro-3,3,3-trifluoropropene

Abstract

The present invention is directed to processes for the production of 1233zd from 240fa and HF, with or without a catalyst, at a commercial scale. The 240fa and HF are fed to a reactor operating at high pressure. The resulting product stream comprising 1233zd, HCl, HF, and other byproducts is treated to one or more purification techniques including phase separation and one or more distillations to provide purified 1233zd, which meets commercial product specifications, i.e., having a GC purity of 99.5% or greater.

What is claimed is: 
     
       1. A process for the manufacture of 1233zd comprising the steps of:
 (a) reacting 240fa and HF in the liquid phase and in the absence of a catalyst in a reactor operating at high pressure to produce a product stream comprising 1233zd, HCl, HF, and other byproducts; 
 (b) distilling the product stream from step (a) into a first overhead product and a first bottoms product rich in HF; 
 (c) distilling the first overhead product from step (b) to form a second overhead product containing HCl and a second bottoms product containing organic components and HF; 
 (d) phase separating the second bottoms product from step (c) to separate the HF from the organic components; and 
 (e) caustic scrubbing, drying, and distilling the organic components from step (d) to provide purified 1233zd; 
 wherein the reactor pressure range is from 150 psig to 600 psig; and 
 wherein the compound 1233zd, produced in step (e) has a purity of 99.5% or greater, as measured using gas chromatography. 
 
     
     
       2. The process of  claim 1 , wherein the reactor pressure range is from 230 psig to 500 psig. 
     
     
       3. The process of  claim 1 , wherein the reactor pressure range is from 350 psig to 450 psig. 
     
     
       4. The process of  claim 1 , wherein the HF from step (b) is recycled to the reactor. 
     
     
       5. The process of  claim 1 , wherein the HCl from step (c) is scrubbed with water and optionally recovered as an aqueous solution. 
     
     
       6. The process of  claim 1 , wherein the HF from the phase separation in step (d) is recycled back to the reactor. 
     
     
       7. The process of  claim 1 , wherein the caustic scrubbing is conducted with NaOH or KOH. 
     
     
       8. The process of  claim 1 , wherein the drying agent in step (e) comprises sulfuric acid. 
     
     
       9. The process of  claim 1 , wherein the drying agent in step (e) comprises molecular sieves. 
     
     
       10. A process for making highly purified HCFC-1233zd by the reaction of 240fa and HF at a reactor pressure of from 150 psig to 600 psig wherein the purification of the HCFC-1233zd comprises the steps of:
 (a) distilling the resulting product stream comprising HCFC-1233zd, HCl, HF, and other byproducts; 
 (b) distilling the overhead product from the step (a) distillation in a second distillation column to remove the HCl; 
 (c) phase separating the bottom stream from the second distillation in step (b) to isolate the HF; and 
 (d) purifying the phase separation bottom layer components from step (c) to yield purified HCFC-1233zd having a purity of 99.5% or greater, as measured using gas chromatography.